Senior Director, Customer Success

Job Description At Transcarent, we’re transforming the healthcare experience by making it simpler, higher quality, and more affordable. We connect people to trusted care through a personalized, technology-enabled experience—helping members and employers navigate healthcare with greater clarity, confidence, and value.

We’re looking for a strategic, commercially minded Senior Director, Customer Success — Mid-Market & Enterprise Account Leader to lead our next phase of customer growth and impact. This leader will own the customer success strategy for a portfolio of mid-market and enterprise clients, strengthen executive relationships, and build the operating discipline required to deliver measurable outcomes at scale.

You will be a trusted advisor to senior client stakeholders and a force multiplier for Transcarent’s account leadership team. You’ll connect customer priorities to our evolving products and services, turn insight into action, and partner across the company to improve retention, adoption, expansion, and member outcomes.

What you’ll do

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* Lead the account leadership strategy. Set the vision, standards, and operating model for mid-market and enterprise customer success across a complex portfolio of employer and healthcare clients.

* Build executive-level partnerships. Establish credibility with CHROs, benefits leaders, CFOs, COOs, consultants, and other senior stakeholders; create executive governance that keeps priorities, decisions, and outcomes aligned.

* Own customer value realization. Ensure every strategic account has a clear success plan, measurable outcomes, adoption milestones, risk mitigation actions, and a compelling value story.

* Drive retention and growth. Partner with Sales, Partnerships, Product, Solutions, Finance, and Operations to protect renewals, identify expansion opportunities, and translate customer needs into commercial and product priorities.

* Strengthen account planning and forecasting. Bring rigor to health scoring, renewal readiness, whitespace planning, escalation management, pipeline visibility, and executive reporting.

* Lead through complexity. Navigate multi-year contracts, diverse stakeholder groups, multiple products and services, implementation dependencies, and high-impact escalations with clarity and urgency.

* Scale the team and the playbook. Coach and develop account leaders, raise the bar on strategic account management, and create repeatable practices that improve consistency without losing the human touch.

* Represent the customer internally. Bring an informed, data-driven customer perspective to leadership and cross-functional forums; influence priorities and remove barriers to customer success.

* Create advocacy. Develop trusted customer champions, references, case studies, and feedback loops that demonstrate the impact of Transcarent’s work.

How success will be measured

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* Improve retention, renewal readiness, and portfolio health across mid-market and enterprise accounts.

* Increase executive engagement and the consistency of strategic account governance.

* Establish a scalable account planning and customer health operating rhythm.

* Improve adoption and realization of customer outcomes across Transcarent solutions.

* Build a strong expansion pipeline in partnership with Sales and Solutions.

* Develop a high-performing team of account leaders through clear expectations, coaching, and career growth.

* Turn customer insights into visible improvements in the product, service, and operating experience.

What you bring

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* 10+ years of experience in Customer Success, strategic account management, enterprise client leadership, healthcare technology, benefits, SaaS, consulting, or a related field.

* 5+ years leading customer-facing teams, strategic account leaders, or a complex enterprise portfolio.

* Demonstrated success improving retention, expanding strategic accounts, and delivering measurable customer or business outcomes.

* Experience working with large employers, healthcare organizations, health plans, benefits consultants, or other complex enterprise buyers.

* Strong executive presence and the ability to influence across multiple levels of an organization—from day-to-day operators to C-suite decision-makers.

* A commercial mindset: 50M+ portfolio accountability. You understand the connection between customer value, adoption, renewal, expansion, and durable revenue growth.

* Strong operating discipline, including account planning, forecasting, risk management, success metrics, and cross-functional execution.

* Excellent written and verbal communication, including the ability to simplify complex healthcare and business topics for different audiences.

* A track record of hiring, coaching, developing, and retaining high-performing teams.

* Comfort operating in a fast-moving, evolving environment where priorities are high-impact and not always fully defined.

You’ll stand out if you have

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* Experience scaling a Customer Success or strategic account management model across multiple market segments.

* Experience translating clinical, operational, utilization, or financial data into an executive-ready value narrative.

* Familiarity with healthcare navigation, virtual care, benefits administration, value-based care, or digital health.

* Experience partnering with Product and Operations teams to influence roadmap, service design, and customer experience improvements.

* A practical understanding of change management and how to drive adoption across complex organizations.

Who we are

Transcarent is the One Place for Health and Careᵀᴹ, bringing medical, pharmacy, and point solutions together with the WayFindingᵀᴹ experience, the first and only generative AI-powered health and care platform for health consumers.

Our WayFinding experience, paired with transparent and consumer-driven pharmacy care, 2nd.MD expert medical opinions, and virtual primary care, works seamlessly with comprehensive Care Experiences – Cancer Care, Surgery Care, and Weight Health – to support people with all of their health needs, simple or serious. More than 1,700 employers and health plans rely on us to provide information, guidance, and care, empowering health consumers with more choice, an experience they love, access to higher-quality care, and lower costs for 21 million Members. For more information, visit transcarent.com, and follow us on LinkedIn.

At Transcarent, our values guide everything we do

* People First: We prioritize our Members, clients, and each other in every decision * Care: Every decision starts with improving health and care for our Members * Resilience: We push boundaries and take the uncharted path to change an industry * Results: We take ownership, solve with speed, and deliver for our people and each other * Humble and Human: We lead with humility, bring fun to tough moments, and go further together

Total Rewards

Individual compensation packages are based on a few different factors unique to each candidate, including primary work location and an evaluation of a candidate’s skills, experience, market demands, and internal equity. Salary is just one component of Transcarent's total package. All regular employees are also eligible for the corporate bonus program or a sales incentive (target included in OTE) as well as stock options. Our benefits and perks programs include, but are not limited to: * Competitive medical, dental, and vision coverage * Competitive 401(k) Plan with a generous company match * Flexible Time Off/Paid Time Off, 13 paid holidays * Protection Plans including Life Insurance, Disability Insurance, and Supplemental Insurance Mental Health and Wellness benefits *

Transcarent is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. If you are a person with a disability and require assistance during the application process, please don’t hesitate to reach out!

Research shows that candidates from underrepresented backgrounds often don’t apply unless they meet 100% of the job criteria. While we have worked to consolidate the minimum qualifications for each role, we aren’t looking for someone who checks each box on a page; we’re looking for active learners and people who care about disrupting the current health and care with their unique experiences. --------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

Department Client Success Location Remote- Remote, Illinois, United States Experience 10 - 16 Years Salary Range USD 165,000 - 175,000 (Annual)